My toolkit: How I've been able to generate a new idea/article every week for a decade

You get the right toolkit, it's amazing what you can build. I can't stop thinking of new ideas for articles because my toolkit is amazingly generative. The kit itself is actually pretty simple though and anyone can have it. Here are most of the tools in it:

Undecideables: It took over 2600 years for logicians and mathematicians to surrender to these. They wanted all propositions to be either true or false. It turns out no matter how hard they tried to come up with rules that would make them one or the other, some statements are neither or both. They're simply undecideable. Take the first such statement to be discovered: "I am lying." If it's true, it's false, if it's false it's true. (See Upleveling)

Self-perpetuating feedback loops: Statements like that have an equivalent in dynamical systems in which parts promote the perpetuation of each other. For example, have you ever had trouble deciding between two options? The basic form is, "I've got to do X, but wait, I can't do X, I've got to do Y, but wait I can't do Y, I've got to do X..." (See Butterfly effect)

Universal tough judgment calls: Undecideables like these fall into a few general categories: Should I join this? Should I stay with this? Can I change this? Is this significant? Should I do what pays now or pays later, Should I say this? Should I fight this? I count only about 15 such questions, not that the number is significant. (See Seven wonderings of the ancient and modern world)

Going meta: When facing an undecideable, what can you do? One possibility is to step out of trying to decide it, to get above it and declare it to be an undecideable. That's what logicians did when they admitted that some statements are neither true nor false. It's also what you do when you say "I can't decide," or what couples do when they stop fighting about who's right long enough to say "Look this is going nowhere." Rather than being within the dilemma, we shift our perspective up a level, to comment about it, declaring it to be a self-perpetuating feedback loop. This up-leveling is called "going meta." See (Rungrunning)

Meta-meta: The levels are limited only by choice. If you disagree about whether it's going nowhere, you can jump up a level more. Not being able to decide whether to decide is a simple example (See Argument Clinic: Monty Python arguing about whether it's futile to be arguing about whether a conversation being had is an argument.)

What's the right level: The question behind all the tough judgment calls we face is about the appropriate level of analysis. For example, take the question, "Should I stay in this relationship?" What's at issue is whether you should resolve to identify with the whole made up of the two of you together, or the whole made up of you alone. It's a question of scale. Or take the question should I do what pays now or later? What's at issue is finding the right level of analysis. Is it the shorter scale of the immediate costs and benefits or the longer scale that includes later costs and benefits. (See granularity)

Yin/yang: The most universal undecideable is whether or not a situation is undecideable. Should you wonder whether to do X or Y, or should you just commit to X and press on, ignoring its disadvantages. One way to think about this is as whether to be within the decision wondering, or above it, where you've made your decision and you're plowing forward. Another, opposite way of looking at it is whether you should be within one of the options, or above that option wondering whether it's right. Either way it's a choice between two neighboring levels. Both of these, however amount to the same choice, between two opposite states, deciding, which demands receptivity, and neutrality, or decided which demands certainty and judgment. This was captured long ago in the difference between yin-receptivity and yang-decisiveness. (See Turing's Blurring Anxiety)